Iron Man 3” has already amassed more than $300 million worldwide and is on target to become the highest grossing opening weekend in the United States ever (outdoing even last summer’s “The Avengers”). This is quite a coup for director/co-writer Shane Black, who, back in the ’90s, during a kind of spec script arms race, was frequently topping himself as the most paid screenwriter of all time, alongside guys like Joe Eszterhas (Black recently told Vanity Fair, in a terrific piece about spec scripts, “Eszterhas used to call and wake me up at night saying, ‘I just sold something for more money than you, ha-ha’”).

Black scripts were known at the time for how well they’re written – they have swift plotting, breezy characterization, and stage direction that compelled the reader to continue (and then offer some staggering sum of money). In that same Vanity Fair piece, Black’s frequent producer Joel Silver said of the spec script boom: “In that period, you could read a script and say, ‘This is a movie. It can be cast. It can go.'” Just like that, many of Black’s scripts went – only, of course, to be changed along the way, sometimes turning something that the studio had paid a handsome sum for into a virtually unrecognizable Frankenstein’s monster. Part of the problem, though, was that while he tried desperately to not be pigeonholed, “a Shane Black script” meant something very specific, and that demand led to a certain amount of creative frustration. Black was both forced out of the game and took himself out willingly, but either way it seemed necessary – he had to dismantle what he had built, just like Tony Stark, in order to triumph again.

His comeback project, a tiny studio gem that he also directed called “Kiss Kiss Bang Bang” that barely anybody saw, starred another Hollywood quantity who was too risky to employ – Robert Downey Jr. Now with the both of them reteaming for what will easily be one of the biggest hits of the year, we thought we’d look back at the screenplays that defined Black as one of the most well-known (and well paid) screenwriters Hollywood has ever known.

the-long-kiss-goodnight-originalThe Long Kiss Goodnight” (1996)
Price: $4 million
Synopsis: An amnesiac schoolteacher discovers that she was once a government-trained assassin. With these newfound memories (and the help of a scummy private detective) she must stop a nefarious terrorist plot.
What About It? At the time of its sale, to New Line Cinema for a whopping $4 million dollars, “The Long Kiss Goodnight” was the most expensive spec sale in the history of Hollywood. (A few years later, Disney bought “Déjà Vu,” which would go on to become a time travel thriller starring Denzel Washington, for an estimated $5 million.) The eventual movie was made by the husband and wife team of Renny Harlin and Geena Davis and Black was originally reluctant to sell it to them, since they had to make one movie before they could begin work on “The Long Kiss Goodnight” – “Cutthroat Island.” Eventually the studio added a half-a-million dollars to the price tag, and Black relented. The original version of the script was more explosively violent, possibly reflecting the post-“Pulp Fiction” permissiveness when it came to mixing grim violence with even grimmer humor. (Brain matter fried on a stove like bacon gristle; in later drafts this element was removed at the request of New Line Cinema.) A number of threads from Shane Black’s filmography, including a Christmas-time setting and at least one character who is a detective (amateur or otherwise), appear in both “The Long Kiss Goodnight” and “Iron Man 3.” The eventual “Long Kiss Goodnight” movie hedged fairly close to Black’s revised draft, but the movie, while attracting an almost instantaneous cult following, never connected with large audience and eventually made less than $90 million worldwide, a shameful showing considering how much better American action movies tend to fare overseas. Its failure also managed to mute Black’s considerable power in Hollywood, leading to a period of inactivity that would last almost an entire decade. Currently, Black is attempting to turn “The Long Kiss Goodnight” into a primetime cable series.

The-Last-Boy-Scout-maxresdefaultThe Last Boy Scout” (1991)
Price: $1.75 million
Synopsis: A former Secret Service agent teams with a former pro football player to investigate the murder of the football player’s stripper girlfriend, uncovering a vast criminal conspiracy.
What About It? At $1.75 million it was also, at that point, the most expensive spec sale ever (67 days later, Joe Eszterhas made double that for his screenplay “Basic Instinct“) and by all accounts that original draft was worth it. Director Tony Scott, many years later, said that he thought the script was better than the movie he made of it – citing the creative tug-of-war between producer Joel Silver and Bruce Willis as the chief reason the movie didn’t perform like it should have. (It has gone on to become one of Scott’s most beloved movies, at least amongst his ardent fans.) Black, who marveled that the scripts bought for the most money were the ones that looked the least like those scripts when the movies finally came out, later described the film as “a frustrating proposition, so much potential, then a lot of ‘big action’ which evolved over time and bloated a much less grandiose blueprint. One of my big Hollywood lessons, not the first.” That’s a good description of the final film – one in which you can see glimmers of the Shane Black script underneath (hardboiled characters, snappy dialogue, bursts of shocking violence, a Christmas setting) but surrounded by a lot of unnecessary bullshit to the point where you can almost feel the egos of the movie superheating the frame and melting away what was once originally there. Tony Stark shares at least some of the edgy paranoia and self-destructive tendencies personified by the two leads of ‘Boy Scout’ (played by Willis and Damon Wayans). “The Last Boy Scout” is an essential piece of Black’s catalog (but far from the best), made all the more so by Scott’s dazzling (if occasionally misguided) direction.